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Synthesis and synthetic applications of 1-metallo-1-selenocyclopropanes and -cyclobutanes and related 1-metallo-1-silylcyclopropanes

  • Alain Krief
Conference paper
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 135)

Abstract

Among the α-heterosubstituted cyclopropylmetals α-selenocyclopropyllithiums represent some of the most valuable synthetic intermediates. They are quantitatively prepared from selenoacetals of cyclopropanones and butyllithiums, are thermally stable at ∼−78° for several hours and are particularly nucleophilic especially towards carbonyl compounds. The cyclopropyl derivatives containing a selenenyl moiety have been transformed to selenium free derivatives such as alkylidene cyclopropanes, vinyl cyclopropanes, allylidene cyclopropanes, cyclobutanones and α-silyl cyclopropyllithiums. The latter compounds have been used as starting material for the synthesis of alkylidene cyclopropanes and cyclopentenyl derivatives. α-Seleno cyclobutyllithiums, which are available in two steps from cyclobutanones, also permit the synthesis of various selenium free homologues such as alkylidene cyclobutanes, vinyl cyclobutanes, oxaspirohexanes and cyclopentanones.

Keywords

Carbonyl Compound Allyl Alcohol Cyclopropane Ring Selenium Atom Synthetic Application 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Springer-Verlag 1987

Authors and Affiliations

  • Alain Krief
    • 1
  1. 1.Départment de ChimieFacultés Universitaires de NamurNamurBelgium

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